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3 bedsNew constructionWith a pool
4 Bedroom Homes in Winter Haven, FL
27 listings

4 Bedroom Homes in Winter Haven, FL

4 Bedroom Homes in Winter Haven, FL

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24 of 27 Listings
Map

4 Bedroom Homes in Winter Haven, FL

24 of 27 Listings

  1. 9 Winterset Dr — photo8Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$430,000

4 bd · 2 ba · 2,489 sqft

9 Winterset Dr, Winter Haven, FL

Jennifer Perez Mojica · LPT REALTY, LLC

  • 822 17th Ter NE — photo31Active

    $379,900

    4 bd · 3 ba · 2,189 sqft

    822 17th Ter NE, Winter Haven, FL

    Jason Stone · BHHS FLORIDA PROPERTIES GROUP

  • 437 Broward Ter — photo32Active

    $390,000

    4 bd · 2 ba · 1,687 sqft

    437 Broward Ter, Winter Haven, FL

    Laura Schmidt · BHHS FLORIDA PROPERTIES GROUP

  • 1380 S Lake Roy Dr — photo46Active

    $395,000

    4 bd · 3 ba · 2,468 sqft

    1380 S Lake Roy Dr, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 405 Valley Ct — photoPrice Reduced88Active

    $465,000

    4 bd · 2 ba · 2,463 sqft

    405 Valley Ct, Winter Haven, FL

    Cannon Kirby · ROOST REALTY GROUP LLC

  • 318 Hamilton Shores Dr NE — photoPrice Reduced58Active

    $533,000

    4 bd · 2 ba · 2,806 sqft

    318 Hamilton Shores Dr NE, Winter Haven, FL

    Dani Borow · KELLER WILLIAMS REALTY

  • 215 Santa Rosa Dr — photoPrice Reduced25Active

    $304,900

    4 bd · 2 ba · 2,355 sqft

    215 Santa Rosa Dr, Winter Haven, FL

    Cynthia Fernandez · XCLUSIVE HOMES LLC

  • 3640 Crump Rd — photo63Active

    $1,399,900

    4 bd · 3 ba · 3,309 sqft

    3640 Crump Rd, Winter Haven, FL

    Amy Reynolds · LOCKHART & ASSOCIATES INC

  • 9469 Waterford Oaks Dr — photoPrice Reduced59Active

    $789,900

    4 bd · 3 ba · 3,648 sqft

    9469 Waterford Oaks Dr, Winter Haven, FL

    Zach Zehnder · KELLER WILLIAMS ST PETE REALTY

  • 5888 Windridge Dr — photo30Active

    $330,000

    4 bd · 3 ba · 2,836 sqft

    5888 Windridge Dr, Winter Haven, FL

    Danique Haywood · MARK SPAIN REAL ESTATE

  • 506 Clayton Cir — photoPrice Reduced26Active

    $309,900

    4 bd · 3 ba · 2,004 sqft

    506 Clayton Cir, Winter Haven, FL

    Anne Halbert · LIVE FLORIDA REALTY

  • 3035 Buckeye Pointe Dr — photo17Active

    $369,900

    4 bd · 3 ba · 2,070 sqft

    3035 Buckeye Pointe Dr, Winter Haven, FL

    Wil Sanders · EXP REALTY LLC

  • 116 Harbor Dr — photo28Active

    $289,900

    4 bd · 2 ba · 1,476 sqft

    116 Harbor Dr, Winter Haven, FL

    Allison McDaniel · XCELLENCE

  • 408 Coleman Dr — photoPrice Reduced32Active

    $389,900

    4 bd · 2 ba · 2,420 sqft

    408 Coleman Dr, Winter Haven, FL

    Michael Mcgee · MAINSTAY BROKERAGE LLC

  • 5009 Strada Dr — photo48Active

    $425,000

    4 bd · 3 ba · 2,434 sqft

    5009 Strada Dr, Winter Haven, FL

    Florentino Beltran · KELLER WILLIAMS ADVANTAGE 2 REALTY

  • 1826 6th St SE — photoPrice Reduced41Active

    $400,000

    4 bd · 3 ba · 2,112 sqft

    1826 6th St SE, Winter Haven, FL

    Daphne Manning · LA ROSA REALTY PRESTIGE

  • 1801 Sandhill Ln — photoPrice Reduced65Active

    $574,900

    4 bd · 3 ba · 2,916 sqft

    1801 Sandhill Ln, Winter Haven, FL

    Emily Cassidy · LAND SOURCE REALTY, LLC

  • 136 Lake Mariam Rd SE — photoPrice Reduced55Active

    $385,000

    4 bd · 3 ba · 2,356 sqft

    136 Lake Mariam Rd SE, Winter Haven, FL

    Jill Baird, LLC · KELLER WILLIAMS ADVANTAGE III

  • 3357 Timberline Rd W — photoPrice Reduced15Active

    $265,000

    4 bd · 2 ba · 1,675 sqft

    3357 Timberline Rd W, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 445 Talamone Dr — photoPrice Reduced57Active

    $519,990

    4 bd · 3 ba · 2,653 sqft

    445 Talamone Dr, Winter Haven, FL

    Jimmy Aguilar · 3D TEAM REALTY LLC

  • 1213 Michelangelo Ln — photoPrice Reduced13Active

    $549,500

    4 bd · 4 ba · 2,894 sqft

    1213 Michelangelo Ln, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 237 Mclean Point — photo86Active

    $720,000

    4 bd · 4 ba · 2,961 sqft

    237 Mclean Point, Winter Haven, FL

    Luis Perez Garcia · EXP Realty LLC

  • 2935 Plantation Rd — photoPrice Reduced53Active

    $563,900

    4 bd · 4 ba · 2,724 sqft

    2935 Plantation Rd, Winter Haven, FL

    Lovett Johnson · LBJ REALTY AND ASSOCIATES LLC

  • 1 Lake Eloise Ln — photoPrice Reduced81Active

    $524,900

    4 bd · 3 ba · 2,550 sqft

    1 Lake Eloise Ln, Winter Haven, FL

    John Carter · KELLER WILLIAMS REALTY SMART

  • 12

    Explore Winter Haven homes

    By price

    • Under $300K
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    By type

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    • With a pool
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    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

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    Listing data & MLS disclosures

    MIAMI REALTORS MLS
    The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
    The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-04-04 00:01:06 UTC
    Stellar MLS
    Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

    Winter Haven, FL community profile

    Population
    58,351
    Median income
    $56,564
    Housing units
    26,800
    People per sq. mi.
    605.3
    Area
    96.4 sq. mi.

    Source: HJN community data

    Winter Haven housing market

    August 2026

    Winter Haven 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 187 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 31, 2026

    Median sale price
    $280,000$204,200–$385,000 typical range
    Price per sq. ft.
    $153
    Sales
    289
    Paid in cash
    45.3%

    Homes on the market · MLS, as of Aug 31, 2026

    Median days on market
    34 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -5.1%